Mono-azodyestuffs



Patented Sept. 22, 1936 Fechenheim, Germany, 'assignor, to' GeneralAniline Works, Inc., New York, N. Y., a corporation of Delaware v NoDrawing. Application October 7,1933, Serial No. 692,700. In GermanyOctober 13, 1932 s 4 Claims, ((11. 260-92) -:This. invention relates tomono-azodyestuffs, more particularly to those corresponding to thegeneral formula:

16 wherein X means V aeyl -,N.. p or N V alk yl phenyl. Y .meanshydrogen; alkylor phenyl, R means acetyl or benzoyl 'andzwherein thephenyl nuclei may contain as substituents methyl or sulfonic acidgroups. H

These dyestufis are obtained by combining a diazo-co' pound of ;an;aromatic amine corre- NH: wherein X means so s l. W

' V alkyl aryl and the benzene nucleus may contain substitucuts, with an2- or 3- or 4-acylamino-8-hydroxynaphthalene-fi-sulfonic acidcorresponding to the formula; r

Hols

British Patents 216,971 and 337,577). In comparison to these knowndyestufis the dyestuffs of the present invention are distinguishedpartly by a better leveling power, partly by a better fastness to light.l

The present invention represents a valuable enrichment of the industry.According to the invention orange to red dyestuffs, are obtained of avery .good leveling power and fastne's's'to light which are especiallysuitable for dyeing animal 1 fibers but may also be used for otherdyeing purposes. v I

The components used maybe varied in such a manner that e. g. theacyl-la'mlno-group contains the following residuesi methyl; -ethyl,{ 15propyl, butyl, benzyl and soon, further 'phenyl and its substitutionproducts. As acylresidues for example acetyl, benzoyl,benzenesulfonyland their substitution products or also the urethanegroup may be named. l 1 i 5 In order toiurther illustrate *myinven'tionf the following examples are given, the parts being by weightand all temperatures in centigrade degrees; but I wish it, howevento beunderstood that my invention is not limited to the exam- 25 ples given,nor to the exact conditions stated therein.

Example 1 ,OH-i 1:1,

and forms a reddish brown water-solublepowder dyeing wool from an acidbath 'very equal red shades which are very fast to light.

The developing may also be carried out in the presence of sodiumbicarbonate or of similar weakly acting neutralizing agents.

N ethyl benzoyl amino-3--'am ino-4-methyl{ benzene yields a moreyellowish red dyvz-rsi'liifi'of a likewise excellent leveling power anda similar good fastness to light.

Dyestuffs of a red shade may'also be obtained by replacing thediazo-compound named in paragraph 1 by the equivalent amounts of thediazocompounds of N (n-butyl) benzoyl-aminolamino-benzene or'N-(p-chloro-benzyl) -benzoylamino--amino-benzene.

Example 2 22.6 parts of N-phenyl-acetyl-amino-4-aminobenzene arediazotized in an analogous manner as described in Example 1. 'Thediazo-solution is developed in an acetic acid medium with the solutionof 29 parts of 2-acetyl-amino-8naphtholfi-sulfonic acid. After isolatingand drying a reddish brown dyestuiT-powder is obtained being easilysoluble in water and dyeing wool very equal red shades fast to light.Itgcorresponds to the following formula:

"'Asimilardyestuff is obtained by using as combining component2-anisoyl-amino-B-naphthol- 6= sulfonic acid. 7

' Example 3 41 8 parts of N-ethyl-acetyl-amino-4-amin0- ben-zene arevdiazotized as usually. The obtained F diazo-sdlutionis allowed to runinto a solution of .35 .parts of -.2-benzoyl-amino-8naphthol-6-sulfQnicacid containing an excess of sodium acetate. After isolating and dryingthe obtained dyestuif forms a reddish brown water-soluble powder dyeingwool from an acid bath very equal red shades which are as to i t- ,I spnds to the i l lfi ant-ice .1 l v -Instea'd -of 2benzoyl-amino-8-naphthol 6-sulfonic acid also its derivatives which are-e. g. sub-e stituteddmthe benzoyl radicalby CH3, OCHs, Cl or 'NOz maybe used. I

' E mp '24 "parts of 'Neethylebenzoyl-amino-4-aminobenzenearediazotized'as described inExample 1 and the obtained diam-solution isallowed to run while cooling into a solution of '29 'partsof '1-acetyl-amino-5=naphthol-7-sulfonic acid containing an excess of sodiumacetate. 'Iheform ed 1 O V I dyestuif represents:-when 1 isolatedanddried ared water-soluble ;;pow,der. rI-t-corresponds to the formula:

can.

andsdye l eanima fi v y V equal red shades be nsstastl q"li ht r Byusing instead of 1-acetyl-amino-5-naphthol-l-sulfonic acid theequivalent amount of 2- benzoyl-amino-8-naph,thol-6-.sulfonic acid, alittle more bluish dyestufi of likewise good fastness qualities isobtained.

More yellowish dyestufis with similar properties may be obtained byusing as combining component e. g. 2-benzoyl-methy1-amino 8-naphthol-6-sulfonic acid or 2-acety1-methyl-amino-8- naphthol-fi-sulfonic acid.

Example 5 20.6 parts of 'N-(n-butyl) -acetyl-amino-4- amino-benzene arediazotized in an analogous manner as described in Example 1. Theobtained .diazo solution is allowed to run into a solution of 29 partsof:2-acetyl amino-5-naphthol-7-sulfonic acid containing an excess ofsodium acetate. The separated and dried dyestuif forms a bright reddishorange colored powder zwhich corresponds to the formula: 1

CHaCO OHaOH2OHaOH2 and dyes wool very equal reddish orange shades fastto light.

A more yellowish dyestufi still faster to light may be obtained by usingas diazo-component the equivalent amount of N-(nebutyheacetyl-aminm4-amino-benzene-2-sulfonic acid.

Example 6 When replacing in Example -1 the-2-acetylamino-8-naphthol-6-sulfonicaeid' by 3-1Ll=partsof 2-(carbethoxy-amino) 8 -naphthol- 6 -sulfonic acid a dyestufi of similarproperties to that obtained according to Example} is obtained whichcorresponds to the followingformula:

S O Nfa 7 I claim:--

1. The mono-azodyestufis corresponding to the general formula HOaSwherein X means acyl acyl -N or N alkyl phenyl Y means hydrogen, alkylor phenyl, R means acetyl or benzoyl and wherein the phenyl nucleicontains a. member of the group consisting of hydrogen, methyl, andsulfonic acid, which dyestuffs dye animal fibers orange to red shades ofa good wherein R1, and R3 mean methyl or phenyl, R2 alkyl or phenyl, R4hydrogen alkyl or phenyl and R5 means hydrogen or a sulfonic acid group,which dyestufis dye animal fibers orange to red shades of a goodleveling power and fastness to light.

3. The mono-azodyestufi of the formula CaHa S O 3N8 which dyestufi formsa reddish brown watersoluble powder dyeing wool from an acid bath veryequal red shades which are very fast to light.

leveling power and fastness to light. 4. The mono-azodyes uff f heformula OH CHr-C 0 /N N= CHs-CHr-CHa-OH:

s OaNa NH0 0 CH:

SOaNa 2. The mono-azodyestuifs corresponding to the general formula OH HR1-CO\ R: l pal-N which dyestufi forms a bright orange colored powderand dyes wool very equal reddish orange shades fast to light.

RICHARD FLEISCHHAUER.

